Sodium Iodide → N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine

HRID 447749Notes

Reaction equation

HRID 447749 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH2:16]([N:15]([CH3:14])[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 690791294-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole

Product 1

HCID 17751624N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.1 g, 0.5 mmol), N-methyl-N-benzylamine (0.07 g, 0.5 mmol), K2CO3 (0.20 g, 1.45 mmol) and a catalytic amount of NaI in DMF (5 mL) is heated to 110° C. overnight. The solvent is removed at reduced pressure, diethyl ether is added to the residue and washed with water. The organic phase is dried and evaporated at reduced pressure and the resulting crude is purified by column chromatography, giving N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine (0.04 g, 0.14 mmol, 28%, oil). (ESI-MS m/z 283 (M+H)+.

Workup

  1. customThe solvent is removed at reduced pressure, diethyl ether
  2. additionis added to the residue
  3. washwashed with water
  4. customThe organic phase is dried
  5. customevaporated at reduced pressure
  6. customthe resulting crude is purified by column chromatography

Sources & evidence

ORD record
ord-cb149c94882848bd882c1aa86324c406
Source dataset
uspto-grants-2013_07
Patent number
US08481567B2

Reaction notes

Loading…